Tetrahydrofuran → 1-[3-Fluoro-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383891

反応式

HRID 2383891 の反応式
C[Si](C)(C)[C:3]([F:6])([F:5])[F:4].C1COCC1.C([O-])([O-])=O.[K+].[K+].[F:20][C:21]1[CH:28]=[C:27]([N:29]2[CH2:33][CH2:32][N:31]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][C:39]=3[CH3:40])[C:30]2=[O:41])[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>CN(C=O)C.C(Cl)(Cl)Cl.CO>[F:20][C:21]1[CH:28]=[C:27]([N:29]2[CH2:33][CH2:32][N:31]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][C:39]=3[CH3:40])[C:30]2=[O:41])[CH:26]=[CH:25][C:22]=1[CH:23]([OH:24])[C:3]([F:6])([F:5])[F:4]

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 596361642-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

生成物 1

HCID 596362271-[3-Fluoro-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one収率 65.92%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

A 0.5M solution of trimethyl-trifluoromethyl-silane in THF (6.68 mL, 3.344 mmol) and K2CO3 (250 mg, 10.82 mmol) was added to 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-121a: 400 mg, 1.337 mmol) in dry DMF (5 mL) under nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by thin layer chromatography (5% MeOH in CHCl3). The reaction mixture was quenched with brine solution and the THF layer was concentrated. The aqueous layer was extracted with chloroform. The organic layer was dried over Na2SO4 and concentrated to get the crude product. Purification by column chromatography on silica gel (2.5% MeOH in CHCl3), followed by hexane wash, afforded 325 mg of the product (65.92% yield).

後処理

  1. customThe reaction mixture was quenched with brine solution
  2. concentrationthe THF layer was concentrated
  3. extractionThe aqueous layer was extracted with chloroform
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto get the crude product
  7. customPurification by column chromatography on silica gel (2.5% MeOH in CHCl3)
  8. washwash

出典と根拠

ORDレコード
ord-ead677956fc940f1bd1b85f509c8c9dc
出典データセット
uspto-grants-2012_09
特許番号
US08263635B2

関連ノート

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